Hydrochloric Acid → 7,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-ol hydrochloride salt

HRID 1513938노트

반응식

HRID 1513938 반응식
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]2[C:3]=1[S:4][CH:5]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:28][CH:27]=1)[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([O:21]S(C)(=O)=O)=[CH:11]2.[OH-].[K+].[Cl-:43].[NH4+].Cl.CCOCC>CO.C(Cl)Cl>[ClH:43].[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]2[C:3]=1[S:4][CH:5]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)=[CH:30][CH:31]=1)[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([OH:21])=[CH:11]2

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 11273238Methanesulfonic acid 7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-yl ester

생성물 1

HCID 670047327,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-ol hydrochloride salt수율 99%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Dissolve methanesulfonic acid 7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-yl ester (5.2 g, 9.0 mmol) in methanol (150 mL). Add potassium hydroxide (5.0 g, 90 mmol) and stir at room temperature. After 4 hours pour into saturated aqueous ammonium chloride and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Dissolve residue in methylene chloride (90 mL) and add 2M HCl in ether (9 mL, 18 mmol). Concentrate in vacuo to yield 4.8 g (99%) of the title compound. LCMS Rt (0.01% heptafluorobutyric acid:1.0% isopropylalcohol:water is mobile phase A and 0.01% heptafluorobutyric acid:1.0% isopropylalcohol:acetonitrile is mobile phase B; gradient method 15 to 95% B, Purity@254 nm)=3.21 min (100%); mass spectrum (ion spray): m/z=504.3 (M+H). Chiral HPLC: 87%.

후처리

  1. extractionextract with methylene chloride
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. concentrationConcentrate in vacuo

출처 및 근거

ORD 기록
ord-340c9335acb44245b8fc500147bec5d1
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217032B2

반응 노트

불러오는 중…